Wingdale Vacation Rentals
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Bedrooms
Bathrooms
Amenities
Suitability
Property type
Distinctive Features
42 rentals in Wingdale.
Welcome to the Lake: Your 4-Season Private Paradise Awaits!
Rental Home
4 bedrooms
3 bathrooms
Sleeps 11
Match: Sleeps
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Lake House Rental On Your Own Private Lake
Rental Home
4 bedrooms
3 bathrooms
Sleeps 11
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3 Bedroom property
Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
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Adorable 3BR-cape near skiing and sledding
Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
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Spacious Log Home, Beautiful Heated, Salt Water Pool and Chef's Dream Kitchen!
Rental Home
5 bedrooms
4 bathrooms
Sleeps 5
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House on Appalachian Trail, walking distance from NYC trains. 3bd/1ba, 3 acres
Rental Home
3 bedrooms
1 bathroom
Sleeps 6
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In town, walk to everything, close to Kent, South Kent and Marvelwood schools
Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
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Charming country house
Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
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Serene, Peaceful Get-Away (Log Cabin by the Lake)
Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
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Family Getaway w/ Fireplace in Sherman on 4 Acres!
Rental Home
6 bedrooms
5 bathrooms
Sleeps 16
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Beautiful mountaintop getaway for peace and quiet
Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
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Silver 1780 Millbrook Classic
Rental Home
5 bedrooms
5 bathrooms
Sleeps 5
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Rustic Country Beach Cottage Candlewood Lake
Rental Home
2 bedrooms
2 bathrooms
Sleeps 2
Match: Sleeps
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Antique Creek-Side Country Cottage With 3.2 Acres
Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
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Millbrook - Beautifully Restored 1840 Colonial Farmhouse - Dutchess Co. NY
Rental Home
6 bedrooms
3 bathrooms
Sleeps 6
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Beautiful Lake House On Peaceful Whaley Lake
Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Stay on an Alpaca Farm
Rental Home
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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Tentrr Signature Site - Maybrook Farm - The Ridge
Rental Home
1 bedroom
1 bathroom
Sleeps 5
Match: Sleeps
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Beautiful Horse Farm
Rental Home
4 bedrooms
3 bathrooms
Sleeps 6
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Litchfield Hills 1790 country cottage
Rental Home
2 bedrooms
1 bathroom
Sleeps 6
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Tentrr Signature Site - Maybrook Farm - The Ridge
Rental Home
1 bedroom
1 bathroom
Sleeps 5
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Campers Paradise, cozy tents, hot showers, free wifi, pet firndly
Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Glamping, Family fun site 2
Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Glamping, family fun, pet friendly
Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Private, Modern Farm Estate Near Candlewood Lake
Rental Home
6 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Victorian Guest Suite in heart of the Village
Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Club Getaway Valley View 1
Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Club Getaway Lake View 2
Rental Home
1 bedroom
1 bathroom
Sleeps 3
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Modern Country Compound w/ guest cottage, pool & sauna! ca. 1790
Rental Home
4 bedrooms
6 bathrooms
Sleeps 14
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Club Getaway Mountain View 3
Rental Home
1 bedroom
1 bathroom
Sleeps 4
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Club Getaway Pine Grove 3
Rental Home
1 bedroom
1 bathroom
Sleeps 4
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Club Getaway Pine Grove 2
Rental Home
1 bedroom
1 bathroom
Sleeps 4
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Fieldstone Farm House on 11 acres, Appalachian Trail, 1.5 hrs outside NYC
Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
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Fabulous 4 Season Resort Home on the Ten Mile River
Rental Home
3 bedrooms
4 bathrooms
Sleeps 10
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Club Getaway Valley View 2
Rental Home
1 bedroom
1 bathroom
Sleeps 4
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Club Getaway Mountain View 2
Rental Home
1 bedroom
1 bathroom
Sleeps 3
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Waterfront House and Artist's Studio in the Woods
Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Club Getaway Valley View 3
Rental Home
1 bedroom
1 bathroom
Sleeps 4
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Club Getaway Mountain View 1
Rental Home
1 bedroom
1 bathroom
Sleeps 4
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Club Getaway Pine Grove 1
Rental Home
4 bedrooms
1 bathroom
Sleeps 4
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Appalachian Country House with Mountain Views
Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Charming Guesthouse in scenic CT town. Bikes, kayaks, firepit, beach pass.
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Showing results 1-42 of 42
Frequently Asked Questions about Wingdale
- Some of the most popular kid friendly rentals in Wingdale are:
- Lake House Rental On Your Own Private Lake
- Welcome to the Lake: Your 4-Season Private Paradise Awaits!
- 3 Bedroom property